21205-24-3

Usage

InChI:InChI=1/C8H8N2O3/c11-9-8(6-10(12)13)7-4-2-1-3-5-7/h1-5,11H,6H2/b9-8+

Upstream product

• 100-42-5 styrene 
• 57354-90-2 5-methyl-3-phenyl-4-nitroisoxazole 
• 27975-80-0 (+/-)-3-bromo-1-phenyl-1-butyne 
• 614-21-1 2-nitroacetophenone 
• 540-80-7 tert.-butylnitrite 
• 66618-68-6 optically inactive (E)-bis-(2-nitro-1-phenyl-ethyl)-diazene-N,N'-dioxide 
• 857555-63-6 3-hydroxyimino-2-nitro-3-phenyl-propionic acid 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 3532-83-0 2-nitro-1-nitrosoethylbenzene 

Downstream Products

• 121246-79-5 C₁₆H₁₂N₂O₅ 
• 614-21-1 2-nitroacetophenone 
• 70976-47-5 5-isobutyl-4-nitro-3-phenyl-4,5-dihydro-isoxazole 
• 124-38-9 carbon dioxide 
• 100-47-0 benzonitrile 
• 65-85-0 benzoic acid 
• 7732-18-5 water 
• 73050-55-2 4-bromo-4-nitro-5-pentafluorophenyl-3-phenyl-4,5-dihydro-isoxazole 
• 7803-49-8 hydroxylamine 
• 70976-40-8 3-Phenyl-5-(m-fluorophenyl)-4-nitroisoxazoline 
• 70976-42-0 5c-(4-iodo-phenyl)-4r-nitro-3-phenyl-4,5-dihydro-isoxazole 
• 62260-72-4 3-phenyl-5,5-dimethyl-4-nitroisoxazoline 
• 62260-76-8 N,N-dimethyl-4-(4c-nitro-3-phenyl-4,5-dihydro-isoxazol-5r-yl)-aniline 
• 62260-77-9 4-nitro-3-phenyl-1-oxa-2-aza-spiro[4.4]non-2-ene 

Relevant academic research and scientific papers

Synthesis and Tautomerization of 2-Nitro-1-nitrosoethylbenzene in Acetone

2-Nitro-1-nitrosoethylbenzene has been synthesized in fairly high yield and its tautomerization studied by 1H NMR spectroscopy.

Synthesis of α-Nitro Ketoximes from Styrenes and tert-Butyl Nitrite

We have discovered that various α-nitro ketoximes can be synthesized in good yields starting from styrenes and tert-butyl nitrite. The success of the reaction was critically dependent on the use of a mixture solvent of dimethylsulfoxide and water. The reaction can tolerate a wide variety of substituents including electron-withdrawing and electron-donating groups.

AgNO3as Nitrogen Source for Cu-Catalyzed Cyclization of Oximes with Isocyanates: A Facile Route to N-2-Aryl-1,2,3-triazoles

A versatile copper-catalyzed [3 + 1 + 1] annulation of oximes and isocyanates with AgNO3 is described. In this conversion, AgNO3 and isocyanates instead of conventional azide or diazonium reagents were used as the nitrogen source. This three-component transformation was achieved by cleaving N-O/C-H/C-N bonds and building CN/N-N bonds, which provides a strategy to prepare N-2-aryl-1,2,3-triazoles with a good substrate and functional compatibility.

Ionic-Liquid Controlled Nitration of Double Bond: Highly Selective Synthesis of Nitrostyrenes and Benzonitriles

Unprecedented in literature, the conversion of aryl alkenes into β-nitrostyrenes (2) or benzonitriles (3) with sodium nitrite can be governed by an appropriate choice of ionic liquid (IL) medium. A general trend was found for the selectivity of these processes, which depends on the nature of IL, with imidazolium-based ILs, such as [Bmim]Cl, that favor the C–H nitration leading to β-nitrostyrenes, while tetraalkylammonium-based ILs, such as TBAA, privilege the C=C bond cleavage affording benzonitriles. Besides a substrate scope, mechanistic hypotheses were provided on the origin of the different selectivity in the two kinds of ILs, based on their own tunable properties such as polarity, viscosity, and solvent cage effects.

Water-controlled nitro-oximation of alkenes under catalyst-free conditions

A convenient and precise nitration and oximation of alkenes with tert-butyl nitrite has been reported, yielding α-nitro ketoximes in satisfactory yields with broad substrate generality and excellent stereoselectivity under mild conditions. Experiments indicate that tert-butyl nitrite serves as both NO and NO2 sources and water plays a key role in this difunctionalization reaction.

Preparation method of alpha-nitro ketoxime derivative

The invention belongs to the field of organic synthesis, and specifically discloses a preparation method of alpha-nitro ketoxime derivatives. The method comprises the steps of taking a styrene derivative of the formula I-1 as a reaction raw material and butyl nitrite as a nitration reagent, adding an assistant, and reacting with water as a solvent under the condition of air at room temperature to obtain the alpha-nitro ketoxime derivative of formula I, has the characteristics of low production cost, mild process conditions, high yield, and environmentally friendly effects, and is very suitable for industrial production. The reaction formula of the method is shown in the description.

Direct synthesis of nitriles from cleavage of C=C double bond with nitrite as the nitrogen source and oxidant

The transformation of the C=C bond of olefin to nitriles has been developed, using easily available NaNO2 as both the nitrogen source and oxidant. Several aryl, heterocyclic nitriles with various substituting groups could be successfully prepared in good to high yields. Based upon experimental observations, a possible reaction mechanism is proposed.

Nitration-Oximization of Styrene Derivatives with tert-Butyl Nitrite: Synthesis of α-Nitrooximes

A highly efficient method for direct nitration-oximization of styrene derivatives using tert-butyl nitrite (t-BuONO) in DMSO was developed. The present method offers a convenient and practical approach for the synthesis of α-nitrooximes in moderate to high yields. The salient features entail mild reaction conditions, metal-free reagent, environmentally benign solvent and simple experimental procedure.

Convenient synthesis of α-nitrooximes mediated by OXONE

A novel OXONE mediated direct difunctionalization of alkenes with NaNO2 in aqueous acetonitrile for the synthesis of α-nitrooximes was developed. The α-nitrooximes were readily prepared in moderate to high yields at room temperature under mild reaction conditions. The present protocol offers an easy and environmentally benign approach to access various α-nitrooximes derived from styrene derivatives.

Synthesis and tautomerization study of pseudonitrosites to 1,2-nitroximes

4-R-Substituted 2-nitro-1-nitrosoethylbenzenes (R = H, CH3, OCH3, Cl, F) have been synthesized under solvent-free conditions and the mechanism of their tautomerization to 2-isonitroso-1-nitro-2-phenylethanes have been investigated by 1H NMR spectroscopy.